5-amino-1,3-dimethyl-1H-pyrazole-4-carboxylic acid | 1342150-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1,3-dimethyl-1H-pyrazole-4-carboxylic acid
• 英文别名: 5-amino-1,3-dimethylpyrazole-4-carboxylic acid
• CAS: 1342150-56-4
• 化学式: C₆H₉N₃O₂
• mdl: MFCD18879234
• 分子量: 155.156
• InChiKey: PSOYXTYCCIWCNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-1,3-dimethyl-1H-pyrazole-4-carboxylic acid 在 氯化亚砜 作用下， 反应 3.0h， 生成 5-Amino-1,3-dimethylpyrazole-4-carbonyl chloride
  参考文献：
  名称：

  Novel Protoporphyrinogen Oxidase Inhibitors: 3H-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives

  摘要：

  A series of 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives were synthesized as candidate herbicides by diazotization of different 5(3)-amino-N-phenyl-1H-pyrazole-4-carboxamide derivatives prepared by the reaction of substituted 5(3)-amino-pyrazole-4-carbonyl chloride with a substituted aniline. Their structures were identified by H-1 NMR and elemental analyses. The isomers D and E were isolated, and their structures were identified by two-dimensional NMR analyses (heteronuclear single quantum coherence and heteronuclear multiple-bond correlation) and single-crystal X-ray diffraction analysis. The bioassay results showed that some of the title compounds exhibited both excellent herbicidal activity at a dose of 93.75 g/ha and strong inhibition against protoporphyrinogen oxidase activity in vitro. The structure-activity relationship showed that D16 possessed the highest activities both in vivo and in vitro when the N-substituted group of the pyrazole ring was allyl and the N-substituted group of benzooxazinone was propargyl.

  DOI：

  10.1021/jf801774k
• 作为产物：
  描述：

  5-氨基-1,3-二甲基吡唑-4-羧酸乙酯 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 5-amino-1,3-dimethyl-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Novel Protoporphyrinogen Oxidase Inhibitors: 3H-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives

  摘要：

  A series of 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives were synthesized as candidate herbicides by diazotization of different 5(3)-amino-N-phenyl-1H-pyrazole-4-carboxamide derivatives prepared by the reaction of substituted 5(3)-amino-pyrazole-4-carbonyl chloride with a substituted aniline. Their structures were identified by H-1 NMR and elemental analyses. The isomers D and E were isolated, and their structures were identified by two-dimensional NMR analyses (heteronuclear single quantum coherence and heteronuclear multiple-bond correlation) and single-crystal X-ray diffraction analysis. The bioassay results showed that some of the title compounds exhibited both excellent herbicidal activity at a dose of 93.75 g/ha and strong inhibition against protoporphyrinogen oxidase activity in vitro. The structure-activity relationship showed that D16 possessed the highest activities both in vivo and in vitro when the N-substituted group of the pyrazole ring was allyl and the N-substituted group of benzooxazinone was propargyl.

  DOI：

  10.1021/jf801774k

文献信息

• [EN] SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES BICYCLIQUES SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE NADPH OXYDASE
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2018203298A1

  公开（公告）日：2018-11-08

  The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)

  本申请涉及取代的融合杂环芳基和杂环化合物，用作烟酰胺腺嘌呤二核苷酸磷酸酶抑制剂（NADPH氧化酶抑制剂），其制备方法，包含这些化合物的药物组合物，以及这些化合物或组合物在治疗或预防由NADPH氧化酶介导的各种疾病、症状和/或障碍中的用途。 (分子式I)
• SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS
  申请人：Glenmark Pharmaceuticals S.A.

  公开号：EP3619209A1

  公开（公告）日：2020-03-11
• Novel Protoporphyrinogen Oxidase Inhibitors: 3<i>H</i>-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives
  作者：Hua-bin Li、You-quan Zhu、Xiao-wei Song、Fang-zhong Hu、Bin Liu、Yong-hong Li、Zi-xia Niu、Pei Liu、Zhi-hong Wang、Hai-bin Song、Xiao-mao Zou、Hua-zheng Yang

  DOI：10.1021/jf801774k

  日期：2008.10.22

  A series of 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives were synthesized as candidate herbicides by diazotization of different 5(3)-amino-N-phenyl-1H-pyrazole-4-carboxamide derivatives prepared by the reaction of substituted 5(3)-amino-pyrazole-4-carbonyl chloride with a substituted aniline. Their structures were identified by H-1 NMR and elemental analyses. The isomers D and E were isolated, and their structures were identified by two-dimensional NMR analyses (heteronuclear single quantum coherence and heteronuclear multiple-bond correlation) and single-crystal X-ray diffraction analysis. The bioassay results showed that some of the title compounds exhibited both excellent herbicidal activity at a dose of 93.75 g/ha and strong inhibition against protoporphyrinogen oxidase activity in vitro. The structure-activity relationship showed that D16 possessed the highest activities both in vivo and in vitro when the N-substituted group of the pyrazole ring was allyl and the N-substituted group of benzooxazinone was propargyl.